I’m just loving the Urban Lumberjack Look! What makes this traditional look so now is this time around it is “Fitted and Slim.” Rugged and Rough is the look but Sleek and Sexy is how you wear it. Boots and bags and coats are the foundation of this look. If this bag is too much of a plaid statement, then look for a red and black buffalo plaid shirt or jacket. This Filson messenger bag is substantial and hot! Filson has been making bags for miners since the gold rush. This is so Americana! Check Mate!
silver fox in the city 
Yes, it is Americana. Years ago, as a kid, I had a jacket with that very plaid and I loved it!!
I don’t know SF – I am not sure about this bag – don’t get me wrong, I have a closet full of Filson’s – but I would never make it out of the house with this bag.
I’m going to have to see how you do it.